Trick or Treat Southport Corridor details for 2025

If you’re looking for fun, costumes, treats, and community spirit this fall, you’ll want to mark your calendar for this one. The vibrant neighborhood of Southport Avenue in Chicago is hosting its annual Trick or Treat on Southport event, and it’s shaping up to be a blast. According to the announcement from the Lakeview Roscoe Village Chamber of Commerce, it will take place Monday, October 27th from 4 PM to 7 PM along Southport Avenue between Roscoe and Grace. 

Here’s everything you need to know — from what to expect, to tips for getting the most out of it.

🕓 Event Basics

  • What: Trick or treating, family-friendly activities, crafts, photo-ops, inflatables, pumpkin patch, music, and more. lakeviewroscoevillage.org
  • When: Monday, October 27th, 4:00 PM – 7:00 PM.
  • Where: Southport Avenue, Chicago — specifically the stretch from Roscoe Street to Grace Street.
  • Weather details: Happens rain or shine, so dress accordingly!

✨ What to Expect

This isn’t just a basic “door-to-door” trick-or-treat — the event brings together dozens of local businesses and organizations with a festive, interactive vibe. Here are some highlights:

  • A pop-up pumpkin patch: Free pumpkins to decorate while supplies last.
  • Inflatables for kids (and maybe big kids) from Lakeshore Sport & Fitness — adult supervision required.
  • A wide variety of activities by neighborhood schools and businesses: balloon artists, face-painting, craft tables, games, and even a pet costume contest.
  • Candy and goodies distributed by participating businesses along the designated stretch of Southport. Check in with stores like Baby Dolls Boutique, Cafe Tola, and many others for extras and special deals.
  • Music and photo-friendly setups — perfect for capturing memorable moments.

🎯 Why It’s Great

  • Community vibe: It brings the neighborhood together in a meaningful, festive way — kids, parents, local businesses, and neighbors all joining in.
  • Local business support: The event is powered by many local small businesses. That means you support the neighborhood economy while having fun.
  • All-ages friendly: Although trick-or-treating is focused on the 4-7 PM window (great for younger children), the event’s atmosphere is welcoming for everyone, including adults and even pets.
  • Convenient location: The stretch from Roscoe to Grace on Southport is walkable and easy to navigate, making it a comfortable outing.
  • Extras beyond candy: Crafts, pumpkin decorating, photo ops, and special offers from stores mean it’s more than just “get a few sweets and go home.”

✅ Pro Tips for You

Since you’ve got your retired time (nice! 😊), you can roll in relaxed and enjoy the scene. Here are a few suggestions:

  • Arrive early: If you want the best parking or a good spot for a photo-op, aim to arrive closer to 4 PM. It will get busier as the evening progresses.
  • Dress for comfort: Since the event is outdoors on a city street, wear comfortable shoes and layer up (Chicago weather in late October can get chilly).
  • Bring a bag or bucket: Whether you’re trick-or-treating or just browsing, having something to collect goodies or grab deals will help.
  • Have a camera/phone ready: Between the inflatables, pumpkin patch, and photo zones, there will be plenty of moments worth capturing.
  • Check a map ahead of time: If you’re driving, knowing where to park or which nearby cross-streets you’ll use can save some hassle.
  • Consider volunteering: If you’re up for it, volunteering can be a fun way to engage, meet neighbors, and contribute to the event’s success. (The event page has a sign-up link.) lakeviewroscoevillage.org
  • Daylight & visibility: By 4–7 PM the light may be fading — especially toward the end — so if you have mobility issues or want to stay more visible, maybe aim for the earlier half of the event.
  • After-event option: Consider grabbing a hot drink or light dinner in a nearby café or restaurant on Southport to extend the outing in a relaxing way.

🎃 What to Bring/What to Know

  • Cash or card: Some stores might have special one-time offers or raffles (check the listings) — worth bringing a card or cash.
  • Weather-check: Even though it’s rain or shine, you’ll want an umbrella or rain jacket if showers are expected.
  • Consent/waiver for inflatables: If you or someone you’re with wants to use the bouncy inflatables, note there’s a waiver and adults must accompany kids.
  • Stay aware of traffic: While the event is on a stretch of Southport Avenue, vehicles may still be moving nearby. Keep an eye on young children near the road.

Leave a comment